1-(2-氨基-3,5-二甲基苯基)-乙酮 | 69976-75-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-氨基-3,5-二甲基苯基)-乙酮
• 英文名称: 2'-amino-3',5'-dimethylacetophenone
• 英文别名: 2-Amino-3,5-dimethyl-acetophenon；2-acetyl-4,6-dimethylaniline；1-(2-Amino-3,5-dimethylphenyl)ethanone
• CAS: 69976-75-6
• 化学式: C₁₀H₁₃NO
• mdl: MFCD11113371
• 分子量: 163.219
• InChiKey: NPBAJZVIRSZENG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-氨基-3,5-二甲基苯基)-乙酮 在 硼烷四氢呋喃络合物 作用下， 以85%的产率得到1-(2-amino-3,5-dimethylphenyl)ethanol
  参考文献：
  名称：

  Acyl Substitution at the Ortho Position of Anilides Enhances Oral Bioavailability of Thiophene Sulfonamides:  TBC3214, an ET_A Selective Endothelin Antagonist

  摘要：

  Sitaxsentan (3, TBC11251) (Wu et al. J. Med. Chem. 1997, 40, 1690) is an orally active ETA selective endothelin antagonist that attenuates pulmonary vascular hypertension and cardiac hypertrophy in rats (Tilton et al. Pulm. Pharmacol. Ther. 2000, 13, 87). It has demonstrated efficacy in a phase II clinical trial for congestive heart failure (Givertz et al. Circulation 2000, 101, 2922). During the discovery of 3, we observed several structure-oral bioavailability relationships. To investigate whether there is any generality in these trends, we synthesized some similar pairs of compounds in the latest series (Wu et al. J. Med. Chem. 1999, 42, 4485) and evaluated their oral properties. In both series, an acyl group at the 2-position of the anilide of these thiophene sulfonamides improved oral bioavailability. As a result of this exercise, TBC3214 (17) was identified as a sitaxsentan follow-on candidate. It is very potent (IC50 for ETA = 40 pM) and highly selective for ETA vs ETB receptors (400 000-fold), with a half-life of >4 h and oral bioavailability of 25% in rats, 42% in cats, and 70% in dogs.

  DOI：

  10.1021/jm000349x
• 作为产物：
  描述：

  2,4-二甲基苯胺 生成 1-(2-氨基-3,5-二甲基苯基)-乙酮
  参考文献：
  名称：

  Processes for the preparation of N-(2-acetyl-4,6-dimethylphenyl)-3-{[(3,4 dimethyl-5-isoxazolyl)amino]sulfonyl}-2-thiophenecarboxamide

  摘要：

  提供了制备N-(2-乙酰基-4,6-二甲基苯基)-3-{[(3,4-二甲基-5-异噁唑基)氨基]磺酰}-2-噻吩羧酰胺的过程，该化合物可用于治疗内皮素介导的疾病。

  公开号：

  US07754892B2

文献信息

• Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole‐4,5‐Diones and Indoline‐2,3‐Diones
  作者：Rong‐Hui Wang、Ya‐Ling Li、Hong‐Jiao He、You‐Cai Xiao、Fen‐Er Chen

  DOI：10.1002/chem.202005081

  日期：2021.3

  The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin‐4,5‐diones and isatins have been developed. In the presence of morpholine‐containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes

  已经开发了对环二酮（包括吡唑啉-4,5-二酮和靛红）的催化对映选择性二有机锌。在含有吗啉的手性氨基醇配体存在的情况下，相应的手性环状叔醇以良好至极佳的收率（高达97％）和对映选择性（高达95％ee）生产。该方案的显着特征包括温和的反应条件，无路易斯酸添加剂和宽泛的官能团耐受性。
• SUBSTITUTED THIOPHENES
  申请人：Gant Thomas G.

  公开号：US20080255036A1

  公开（公告）日：2008-10-16

  Disclosed herein are substituted pyrimidine-based endothelin modulators of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.

  本文揭示了一种基于嘧啶的Formula I内皮素调节剂的替代物，其制备方法，药物组合物以及使用方法。
• Sulfonamides for treatment of endothelin-mediated disorders
  申请人：——

  公开号：US20020091270A1

  公开（公告）日：2002-07-11

  Thienylsulfonamides and their pharmaceutically acceptable derivatives, pharmaceutical compositions, articles of manufacture, combinations, lyophilized powders and methods for the treatment of endothelin diseases using these formulations and sulfonamides are provided. A process of preparing an alkali metal salt of a hydrophobic sulfonamide is provided. The process includes the step of dissolving a free sulfonamide in an organic solvent in the presence of a saturated alkali metal salt solution and recovering the formed sulfonamide salt from the organic phase.

  提供了噻唑磺胺及其药用可接受衍生物、药物组合物、制造物品、组合物、冻干粉剂以及使用这些配方和磺胺类药物治疗内皮素疾病的方法。提供了一种制备疏水性磺胺类化合物的碱金属盐的过程。该过程包括将游离磺胺类化合物溶解在有机溶剂中，在饱和的碱金属盐溶液存在下，并从有机相中回收形成的磺胺类盐的步骤。
• PROCESS FOR PRODUCTION OF 4-OXOQUINOLINE COMPOUND
  申请人：Matsuda Koji

  公开号：US20090318702A1

  公开（公告）日：2009-12-24

  The present invention provides a compound useful as a synthetic intermediate for an anti-HIV agent having an integrase inhibitory activity, a production method thereof, and a production method of an anti-HIV agent using the synthetic intermediate. Specifically, the present invention provides, for example, compounds represented by the formulas (6), (7-1), (7-2) and (8): wherein R is a fluorine atom or a methoxy group, R 1 is a C 1 -C 4 alkyl group, R 2 is a hydroxyl-protecting group, and X 2 is a halogen atom, a production method thereof, and a production method of an anti-HIV agent using the synthetic intermediate.

  本发明提供了一种化合物，可用作具有整合酶抑制活性的抗HIV药物的合成中间体，其生产方法，以及使用该合成中间体制备抗HIV药物的生产方法。具体来说，本发明提供了例如由以下公式表示的化合物（6），（7-1），（7-2）和（8）： 其中R为氟原子或甲氧基，R1为C1-C4烷基，R2为羟基保护基，X2为卤原子，其生产方法，以及使用该合成中间体制备抗HIV药物的生产方法。
• Primary amino acid catalyzed asymmetric intramolecular Mannich reaction for the synthesis of 2-aryl-2,3-dihydro-4-quinolones
  作者：Buddhadeb Mondal、Subhas Chandra Pan

  DOI：10.1039/c4ob02146k

  日期：——

  Primary amino acids are found to be good enantioselective catalysts for the direct asymmetric Mannich reaction between 2-amino acetophenone and aldehydes. The 2-aryl-2,3-dihydro-4-quinoline products are obtained in moderate to good yields and good to high enantioselectivities with 10 mol% of the primary amino acid catalyst under mild reaction conditions.

  发现伯氨基酸是2-氨基苯乙酮与醛之间直接不对称曼尼希反应的良好对映选择性催化剂。在温和的反应条件下，以10摩尔％的伯氨基酸催化剂以中等至良好的收率和良好至高的对映选择性获得2-芳基-2,3-二氢-4-喹啉产物。